Trifluoroacetic acid → HCID 44404226, compound

HRID 1747698Notes

Reaction equation

HRID 1747698 reaction equation
C(OC([N:8]1[CH:12]2[CH2:13][CH2:14][CH:9]1[CH:10]([C:15]1[CH:16]=[N:17][C:18]([F:29])=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=3)[CH:20]=1)[CH2:11]2)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[NH4+].[OH-]>C(Cl)Cl.O>[C:27]([C:24]1[CH:23]=[CH:22][C:21]([C:19]2[CH:20]=[C:15]([CH:10]3[CH2:11][CH:12]4[NH:8][CH:9]3[CH2:14][CH2:13]4)[CH:16]=[N:17][C:18]=2[F:29])=[CH:26][CH:25]=1)#[N:28]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 89655578HCID 89655578, compound

Product 1

HCID 44404226HCID 44404226, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 16 (275 mg, 0.7 mmol) was dissolved in anhydrous CH2Cl2 (3 mL) and cooled in an ice-water bath. TFA (3 mL) was added in 30 min. After stirring at room temperature for 1 hr, the mixture was poured into a cold solution of NH4OH in water (1:1). The mixture was then extracted with CH2Cl2. The organic phase was washed with brine then dried over anhydrous Na2SO4 and evaporated to dryness. After flash chromatography on a silica gel column with CH2Cl2-MeOH, the free base was isolated as a clear oil (200 mg, 93%). 1H NMR (CDCl3): δ (ppm) 1.5-1.7 (m, 5H), 1.8-1.9 (m, 1H), 2.84 (dd, 1H, J=5.1, 9.0 Hz), 3.61 (br s, 1H), 3.82 (m, 1H), 7.6-7.8 (m, 4H), 8.09 (dd, 1H, J=2.4, 6.6 Hz), 8.14 (m, 1H). 13C NMR (CDCl3): δ (ppm) 29.6, 30.7, 31.9, 40.9, 44.6, 56.8, 63.2, 112.3, 118.9, 121.5 (d, J=112.2 Hz), 129.9 (d, J=13.2 Hz), 132.7, 139.3, 140.1, 141.6, 146.5 (d, J=57.9 Hz), 157.5, 160.7.

Workup

  1. temperaturecooled in an ice-water bath
  2. extractionThe mixture was then extracted with CH2Cl2
  3. washThe organic phase was washed with brine
  4. dry with materialthen dried over anhydrous Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-aced16b7ba7744138a98ecb1f8edb3c6
Source dataset
uspto-grants-2015_10
Patent number
US09150581B2

Reaction notes

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